The Masterless People: Pirates, Maroons, and the Struggle to Live Free

In the “bizarre and horrifying world” of the early modern Caribbean, maroons and pirates both prized their freedom above all else. And sometimes they worked together to safeguard it.

Joseph Kelly | an excerpt adapted from Marooned: Jamestown, Shipwreck, and a New History of America’s Origins | Bloomsbury | October 2018 | 16 minutes (4,192 words)

The English word maroon did not yet exist in 1607. The Spanish word from which it derives, cimarrón, was first coined to describe domesticated cattle brought to Hispaniola that escaped into the wild parts of the island. Most scholars today accept some form of this derivation, which dates at least to 1535, just forty years after Columbus landed on Hispaniola. By 1540, cimarrón was applied to Africans who, like the chattel before them, fled to the remote, wild places behind Spanish coastal colonies. Maroon first appeared in English in 1666 when John Davies, translating a history of Barbados, wrote that slaves, like those animals, would “run away and get into the Mountains and Forests, where they live like so many Beasts; then they are call’d Marons, that is to say Savages.” Sometimes, these escapees formed new communities in the wilderness, a phenomenon that anthropologists call grand marronage. Cimarrón and eventually the shortened word, maroon, carried a heavy metaphoric or perhaps even literal sense that these fugitives devolved to an animal ferocity, wildness, and savagery. That is to say, they left civilization to live like Native Americans.

Indians were often midwife to marronage. Siouan tribes or Yuchi Indians living on South Carolina’s coast helped the first maroons on the soil of what is today the United States. In 1526, five hundred Spanish with one hundred African slaves settled near the mouth of the Pee Dee River. The summer “seasoning,” mosquito-borne illnesses like yellow fever, began to carry off the settlers. In the midst of this crisis, several slaves escaped into the hinterland, taking refuge among the Indians, and when in October the 150 surviving Spanish abandoned the settlement and sailed for Hispaniola, they left behind those escapees. Eighty years before Jamestown, the first intercontinental settlers on the East Coast of the United States were maroons: Africans who had escaped Spanish slavery.

Although maroons escaped from slavery, it was no Exodus. No God tendered them a land of milk and honey as reward for keeping faith. They retained no orthodox hegemony. They were heterodox. Typically, they came from various districts in Africa, and although they might share a creole language and common suffering, they shared little else. They entered no promised land. The wildernesses to which they fled were not their natural element, though the Europeans often thought they were. The mountains of Jamaica were just as inhospitable to Africans as they were to Europeans. The jungles of Suriname and the swamps of Carolina posed the same dangers for blacks as for whites. These places terrified the escaped slaves as they would terrify you or me were we suddenly hurled into them with only the resources we could steal and carry. Maroons embraced these dangers in desperation, preferring them to the certain dangers and degradations of slavery. They pledged faith to each other, formed communities according to their own liking, and kept sacred above all else the principal of freedom.

Eighty years before Jamestown, the first intercontinental settlers on the East Coast of the United States were maroons: Africans who had escaped Spanish slavery.

According to the anthropologist Richard Price, even hundreds of years after their escape from bondage, “freedom” still defines maroon communities. Choosing freedom is the pillar of their identity. Maroons are the people who escaped slavery; who braved the snakes and alligators and cats of jungle, swamp, and mountain; who had the courage to risk the retributive torture of pursuing whites — all for freedom. Maroon identity, Price tells us, “is predicated on a single opposition: freedom versus slavery.” No other mode of society identifies so strongly with the unalienable human right of self-determination.

To borrow a title from the naturalized American, Christian existentialist Paul Tillich, maroons display better than anyone the Courage to Be. Martin Luther King Jr. wrote his dissertation on the philosophy of Paul Tillich and applied it to the existential experience of African Americans. Suffering under the penal laws of Jim Crow, they valued freedom as the defining human identifier. And so, in his “Letter from a Birmingham Jail,” MLK, quoting Tillich, identifies segregation as an existential crime and, borrowing from Saint Thomas Aquinas, defines unjust laws as those degrading the human personality. Scholars are just beginning to catch on to how important maroons are to our conception of freedom. The philosopher Neil Roberts, for instance, suggests that marronage exemplifies the “supreme ideal of freedom” and that to understand “freedom” we must understand the psychological experience of flight from bondage and the subsequent reconstruction of civil society. For Roberts, the maroon is the lens through which we can understand freedom, which is not a static condition but “perpetual, unfinished, and rooted in acts of flight.” In this spirit, Isaac Curtis studies the “masterless peoples” of the historic Caribbean, not only maroons but also pirates. These societies were “remarkably egalitarian” on the whole and sometimes democratic, especially compared to the societies from which maroons escaped and pirates plundered. In the “bizarre and horrifying world” of pirates, Sarah and Paul Robinson write (perhaps too enthusiastically but with general accuracy), “genuine democracy flowered, far beyond what existed in the budding democracy movement of the day.” And Sylviane Diouf’s Slavery’s Exiles: The Story of the American Maroons has begun to nudge historians towards recognizing that maroons — “people in the hidden wilds” — are central to our history.

The first Englishman to meet a genuine maroon was a red-bearded corsair not yet thirty years old. Cruising the coast of Spanish Panama, he hoped to loot the mule trains that hauled heavy bars of Peruvian silver over the isthmus for loading on the treasure ships. In 1572 this pirate was better known in Panama than in his native Plymouth. His name swept up and down the coast and carried eventually inland, via murky lines of communication, from the mouth of one slave to the ear of another, till finally it reached the villages of a mysterious people living in the impenetrable jungles of Panama’s interior. His notorious enmity for the Spanish made these maroons (or Symerons, as they were called in the narratives) seek out the obscure sailor from Devonshire, the man known as Francis Drake.

Drake lived with the Symerons for months. He admired their remarkable woodcraft as they stalked the Spanish convoys. He fought side by side with them till finally he got his silver and the maroons got their iron, a metal far more valuable to people carving a society out of the wilderness. For a time Drake’s maroons were crucial to England’s overseas strategy, the linchpin of a plan drawn up by an Oxford cosmographer named Richard Hakluyt. Under English protection and transported by Drake, hundreds of maroons disappeared at Sir Walter Raleigh’s settlement at Roanoke, yet another mystery of the “lost” colony. A generation later the very same Richard Hakluyt, by then an old man, was one of the few names on the Virginia Company’s charter. Although liberated slaves were no longer at the center of England’s plans for America, Jamestown produced its own maroons: white Englishmen escaping the slave-like conditions imposed by the joint-stock corporation that governed them.

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Columbus established a permanent Spanish colony on Hispaniola in 1493. He first touched the coast of Panama on his fourth and last voyage in 1502, seventy years before English ships sailed those waters. By 1510, Spaniards began their conquest of Panama. In 1513, Balboa, crossing the isthmus, saw the Pacific Ocean. In 1520, Magellan found a sea route into that ocean around the southern tip of the continent. Pizarro garroted the Incan emperor Atahualpa, in 1533 and immediately set about the business of fleecing Peru of gold and silver. When the Incan riches were looted, Spain used American, then African, slaves to work the mines. They shipped the lucre of this foul industry up the Pacific coast to Panama. Trains of fifty to a hundred mules plunged into the jungle, carrying the treasure to Venta Cruz, a depot just over the continental divide, where the treasure was loaded onto river boats and floated down to Nombre de Dios, the Atlantic seaport where, finally, it was loaded onto great ships that carried the bars of silver and gold in convoys to Spain. French pirates started raiding the Caribbean shipping almost right away, so by the time the English tried to get in on the action it took ingenuity as well as daring to pry this loot from the Spanish.

Francis Drake had plenty of both. The age suited him. He exemplifies that entrepreneurial energy unleashed by Queen Elizabeth’s new, partially meritocratic society — energy that had lain dormant for generations under rigid hierarchies. Capitalism was walking on the lanky, jointy, and clumsy limbs of its adolescence, running wild all over the globe, round the Horn of Africa, across the mysterious Atlantic, and finally round South America’s treacherous wave-raising windy cape into the Pacific. Those historians of class conflict, Marx and Engels, thought that these oceanic explorers triggered the modernization of Europe. Capitalism “sprouted from the ruins of feudal society” only when ships opened up trade routes — and markets — between societies hitherto isolated from each other. One does not need to be a Marxist to agree that these bold mariners had to come before factory owners. Before new commodities and new means of producing commodities could be invented, the explorers had to open markets.

Freedom is not a static condition but ‘perpetual, unfinished, and rooted in acts of flight.’

Drake grew up in a two-room “longhouse”: a typical sixteenth-century English farmhouse with a central chimney flanked on either side by a single room with a loft. One side of the chimney belonged to the animals, while the other belonged to the farm’s people. Francis spent his young life in this fifteen-by-fifteen-foot square, or in the loft above it, or in the fields and lands surrounding the Drake family’s couple of hundred acres. They were not peasants. They were yeoman farmers, prosperous by the standards of the day, gaining in each generation. Francis’s father, Edmund Drake, was an educated man, an ordained a minister. Nevertheless, the Drake family ate a peasant’s plain, hearty diet of bread, “peas and beans, greens, parsnips, turnips, carrots, and beets . . . milk, butter, cheese . . . chicken and eggs . . . apples, plums, and berries.” Beer was another staple, and the local variety was an oat beer that outsiders found undrinkable. Had Drake been born in 1440 instead of 1540, the smell of soil and cows would have saturated his hair and clothes his entire life. But their fields were near Plymouth, and Francis could smell the salt air of the sea. Edmund Drake sent Francis to Plymouth to train in the house of a kinsman, William Hawkins, a prominent merchant in that seafaring town.

In 1562, William’s son, John Hawkins, sailed four ships from Plymouth to Sierra Leone, where he took a cargo of “blacks, stealing some from Portuguese traders, capturing others on his own, and finally taking a Portuguese vessel to carry the slaves that could not be crammed into his own holds.” Then they sailed for the Spanish West Indies. Spain forbade its colonies from trading with the English, and so the proffering of slaves was highly irregular and purchases were often accompanied by violence. There was a good bit of extortion in this early version of what American schoolchildren call the “triangular trade.” Plymouth merchants emptied their cargoes of English textiles in the Canaries and Africa, often doing so illegally. In Africa, they filled their holds with slaves, bargained for illegally or simply snatched from villages within raiding distance of the coast. They smuggled this human cargo into the Spanish West Indies, where they filled their ships once again with whatever loot they could procure or steal from Spanish colonists.

Drake’s first true pirate cruise made enough money in Panamanian waters to finance his second cruise in 1572. The small Pascha (forty tons) and the tiny Swan (twenty-five tons) menaced the Atlantic coast, making the ambivalent gestures regarding trade (tin, pewter, and cloth) that were necessary to pretend that any thieving they did was not piracy but a defense of open markets. The Spanish refused their commerce. Drake forced them to “trade” at gunpoint. He raided the main seaport, Nombre de Dios but found it was the wrong season for plucking treasure. Even so, the locals defended it valiantly, and Drake lost several men and had to be carried himself, bleeding, back to the pinnaces.


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The incident demonstrates Drake’s character, which was not far from Hollywood’s idea of a Caribbean swashbuckler. Neither short nor tall, he was somewhat stocky and fair-haired, altogether an average-looking Englishman. But he had the air of “forceful” authority and a reputation for firm command. He was “feared and obeyed by his men,” according to a Spanish witness, a gentleman prisoner who observed him closely. “Alert, restless, well-spoken, ambitious, vainglorious,” the Spaniard wrote, “but generous and liberal; not a cruel man.” He could be mild and generous to prisoners, but on at least one cruise he carried a kidnapped woman to his sea cabin. He had little ideology: like a good entrepreneur he was governed by profit. His personal bravery was both a virtue and a defect. It proved his valor to his men, but it robbed him of discretion. He smiled carelessly at the enemy’s sword and musket, as if addicted to the excitement of the melee, where treasure and death were equal chances. Or not quite equal. He did try to stack the odds in his favor by a bold stroke or ambush. But he loathed the clerkish work of meticulous planning, so he hacked at details like a machete cutting a path from tangled vines. Sometimes his improvisations seemed providential. Luck hovered over him like a guardian angel. But some of his capricious decisions were self-defeating and got himself and his men into fixes. The smaller his crew, the more effective his leadership. He admiraled a naval fleet like a pirate would, with too keen an eye to his own affairs and too little attention to the state’s. He never knew if the queen was going to be pleased or mad about his latest exploit.

In 1572, when Drake captured a coasting vessel off Panama, he would rifle the cargo, put the Spanish ashore, and pump the slaves for intelligence. They told him stories about people living in the dense jungles and rugged mountains of the country. Bands of escaped slaves, whole towns full of Africans, were hiding in the rugged Panamanian interior. They were a nation of outlaws living within a stone’s throw of the Spanish colonies, yet in near-total isolation from those outposts of civilization. Even as Drake learned about these Symerons, or “wild men,” the Symerons heard rumors about him. Drake’s name was “most precious and honoured” among them because he harassed the Spanish, and no one hated the Spanish more than Panama’s Symerons.

Escape was the purest form of resistance. By the mid-1500s, bands of fugitives were living just beyond the borders of every colony.

They had very good reason. Spain’s treatment of Native Americans was amazingly cruel. Back in 1492, Columbus brought a few natives to Spain, baptized them in Guadalupe, and paraded them around Seville, which helped stir up interest in his second voyage to the Americas, seventeen ships ferrying more than a thousand men and farm animals. So the slaughter of Americans began. The cruelties performed by Spanish settlers defy the comprehension of anyone with a belief in humanity. With gunpowder and metal and armor, the Spanish could do whatever they wanted to the natives, despite the imbalance in numbers. Civilization was an ocean away. No hand in Hispaniola would stop them, certainly not the admiral and governor, Christopher Columbus. Soldiers roamed the countryside slaughtering, raping, maiming people with no apparent motive other than to satisfy some sadistic pleasure. Some babies they fed to fierce war dogs in front of their mothers. Others they took by the ankles and swung round to bash their heads against rocks. Soldiers tested the sharpness of their swords by disemboweling their prisoners. Columbus ordered that natives who provided too little gold should have their hands chopped off. These details come to us from Bartolemé de las Casas’s Short Account of the Destruction of the Indies. His father was with Columbus on the second voyage, and Bartolemé himself came to Hispaniola in 1502. He reported, for example, that he had seen the Spanish tie “native leaders and nobles . . . to a kind of griddle consisting of sticks resting on pitchforks driven into the ground and then grill them over a slow fire, with the result that they howled in agony and despair as they died a lingering death.” He witnessed several chiefs tortured in just this manner.

Naturally enough, the Indians “took to the hills to get away from the brutal and ruthless cruelty that was being inflicted on them.” In the Spanish reckoning, this was theft. Runaways were hunted by mastiffs, dragged back, and condemned by kangaroo courts before suffering their inevitable and often fatal flogging. Within a generation, sadism, disease, overwork, and starvation depopulated the once-thriving indigenous communities of Hispaniola. Tens of thousands died in a year. Cubans and Bahamians were enslaved to replace the dead of Hispaniola, but these did not suffice, and within a quarter century the Spanish had “effectively liquidated . . . the Caribbean’s millions of native people.” As early as 1510 they began importing Africans.

This pattern was repeated all over the New World. As quickly as the Spanish and Portuguese erected the horrifying apparatuses of their slave societies, slaves sought refuge in the hinterlands. Escape was the purest form of resistance. By the mid-1500s, bands of fugitives were living just beyond the borders of every colony: Peru, Honduras, Venezuela, Brazil, Cuba, Santo Domingo, Panama. They hid in the inhospitable hinterlands: mountains or swamps or jungles where pursuit was dangerous and uncertain. These bands, called maroons, might operate as brigands, raiding plantations for supplies, or they might attempt total self-sufficiency in their isolated territories. Their design was to never return to “civilization.”

In 1525 slaves first escaped Spanish settlements in Panama and took off for the dense forest, from which they occasionally raided plantations for supplies. They were hunted down and killed. But the cruelties of slavery insured a perpetual cycle of revolt, flight, and recapture. For twenty-five years, various groups of slaves repeated the pattern of escape, freedom, recapture, death. In 1549 a man named Felipillo led a more successful flight of escapees, who managed to build a village and re-create what the historian Ruth Pike, drawing on contemporary Spanish accounts, calls the “African way of life” they had left behind, although truly that must have been a creole culture derived from several places in Africa. They lived free for two years, periodically harassing the Spanish, until the village was discovered, attacked, and burned, and Felipillo was captured and executed. Several in his community avoided recapture, rebuilt the village, and became the seed of the most successful maroon community in Spanish America. Within a few years about eight hundred cimarróns or Symerons — escaped slaves melded with the remnants of Panamanian indigenes — congregated under the leadership of a “strong good-looking man” named Bayano, a “king” obeyed and feared by his followers. As many as three thousand slaves escaped into the “long chains of high and jagged mountains” of the interior, where they built and fortified their villages and “lived a free life based on African tribal customs.” At the height of his powers, Bayano ruled over at least forty lesser chiefs.

Drake first made contact with the Symerons in September 1572. Twelve black men came down out of the mountains to ally their people with Drake. The Symerons joined the pirates in their island hideout, showed the English how to build houses out of palmettos, and helped construct a European-style fort. The Symerons were armed with bows and four types of arrows. The heaviest were large-game arrows with heads of iron sharpened to a knife’s edge and weighing one and a half pounds, which made “so large and deep a wound . . . as can hardly be beleeved of him that hath not seen it.” Lighter arrows were for birds. For killing men, they had arrows longer than those made famous by Scottish bowmen and tipped with iron, wood, or even fish bones.

Through late autumn, the Symerons kept the English supplied with fresh meat from wild hogs and pheasants and fresh vegetables that they rooted out of the woods. But gradually their failure to steal any big treasure demoralized the English. One of Drake’s own brothers, John, died in an impetuous raid on a frigate that the Spanish ably repulsed. Then their health flagged. In January 1573 a mysterious “calenture” infected half the men, and the English were carried off, one by one, until the survivors were tempted to despair. Among those stricken was another Drake, young Joseph, who died in his brother’s arms. On top of this came the news that the powerful Spanish naval fleet, which would convoy the treasure ships, had arrived in Nombre de Dios. Such a powerful force seemed to dash their last hope for plunder. Twenty-eight were dead. Only thirty or forty English were left, and none wanted to continue risking their lives for the trifles they took from the few boats they succeeded in seizing. Drake knew he had to try some bold stroke. If fighting the way pirates fought was not working, why not try the ways of Symerons?

On Shrove Tuesday, February 3, 1573, a company of forty-eight men — eighteen Englishmen and thirty Africans — headed into the wilderness. The English carried their own weapons, while the Symerons carried provisions, which they augmented by hunting wild pig and otter. Along the way they gathered wild mammeas, guavas, oranges, lemons, and something they called “pinos.” Every evening, the Symerons built sturdy, watertight houses out of palmetto boughs and plantain leaves. On the third day they stepped out of the trees into a town of fifty or sixty houses arranged on three pleasant streets, where the Symerons lived “very civilly and cleanely,” bathing in the river, wearing clothes “very fine and fitly made.” These families grew crops and raised fowl and animals, and as marvelous as this sight was to the English, the Africans told them of another town — a veritable city — where their king lived with seventeen hundred “fighting men.”

The next day the pirates and Symerons resumed their march into the trackless woods. Four blacks scouted the way about a mile ahead of the main group, breaking boughs to mark the route; then came twelve Symerons warriors; then the English with two Symerons captains keeping them quiet; and finally a rear guard of another twelve maroons. They were climbing, and the high trees provided shade, and the undergrowth thinned out, so that the march was easy and cooler than an English summer day. At about ten in the morning on the eleventh of February, they came upon an open space cleared of trees and dotted with shelters that the Symerons had built for travelers. Maroons from “diverse places in those waste Countries” frequented the spot. A Symeron leader named Pedro took Drake by the hand and led him to a tall, broad tree growing from the very spine of the ridge. Steps had been carved in its trunk. Up high in the branches a platform could accommodate a dozen men, and Pedro took his guest up this height. A breeze was blowing. A few clouds hung in the blue sky, too few to obscure the view. To the north, Drake could see the Atlantic Ocean whence they had come, miles off in the distance but spreading to the curved horizon — an impressive view, but something that could be seen, after all, from the heights of Drake’s hometown on the Devon coast. But when he turned around he witnessed what few white men ever had, what he called the “South Atlantick” and some called the “South Sea”: the Pacific Ocean. The poet John Keats described the feeling when a Spanish explorer with eagle’s eyes stared at the Pacific, and his men in wild surmise stood silent upon that peak in Darien. So were the English awed.

After a minute Drake regained his composure. If it pleased “Almighty God of his goodnesse,” he whispered, give him “life and leave to saile once in an English Ship in that sea.”

One of his lieutenants, John Oxnam, stood by his side and replied that unless Drake “beat him from his Company,” Oxnam “would follow him by Gods grace.”

Whether by God’s leave or not, Drake got his treasure. They ambushed one of those caravans carrying bars of silver overland from the Pacific to the Atlantic. The Symerons cared for none of it: they wanted only iron, which Drake gave them gladly. And Drake got to launch his famous career.

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Joseph Kelly is a professor of literature at the College of Charleston. He is the author of America’s Longest Siege: Charleston, Slavery, and the Slow March Toward Civil War, and the editor of the Seagull Reader series. He lives in Charleston, South Carolina.

Longreads Editor: Dana Snitzky